Five Reasons to Book a Small Group Private Tour

At Chicago Detours, we offer all kinds of small group private tours by foot and by car, in downtown and in our Chicago neighborhoods. “Small” can get a bad rap, especially in the city of “Big Shoulders,” super tall skyscrapers, almost three million people and one Great Lake. At Chicago Detours we know that even if you have just a small group of people – which for us is eight or fewer tour guests – small can still be powerful! Dynamite, as they say, comes in small packages. A dynamic small group private tour could be perfect for a small family outing or corporate event.

We are one of only a few tour companies in Chicago who believe in the value of working with small groups – not just big buses. In fact, we love working with small groups for our private tours. Here are five reasons you should consider booking a small group private tour for an awesome exploration of Chicago architecture and history. 

1. You want some QT with your favorite city AND your favorite people

Public group tours are great for meeting new people. For times when traveling is more about connecting with your travel companions though, a small group private tour is ideal. On a small group private tour, you don’t travel with strangers. The tour group comprises just you and up to seven other people of your choosing. It’s like you get to make your own exclusive Chicago architecture club for the day, and you’re the president.

On the other hand, maybe your favorite person is just yourself. A small group private tour can be as small as just you and an experienced tour guide. Remember when I said public tours are great for meeting new people? Well, if the phrases “big”, “public”, and “new people” raised your introvert hackles, what could be better than getting all of the educational, instaworthy benefits of a Chicago Detours experience without all the other humans? (For the record, our public walking tours of interior architecture, historic bars, and Chicago neighborhoods tend to attract good people.)

Private Tour Chicago Pilsen Books
You can spend a little extra time where you really want to, like at Pilsen Community Books on our Changes and Spaces in Pilsen Walking Tour. Photo by Pawel Skrabacz.

2. You want the tour all to yourself

Maybe you were the kid who always raised their hand in class. Maybe you’re easily distracted. Of course, we think every tour guest is very special. But as the only guest(s) on your small group private tour, you will have the guide’s undivided attention. Ask as many questions on Chicago architecture and history as your curious heart desires with us.

3. Explore stories and places locals don’t know

A small group private tour allows you to get up close and personal with our tours, which are already about digging into the deeper story of Chicago. While we offer a “Detour 101 Highlights Tour” for Chicago newbies or those with limited time, our specialty tours will show you a whole new perspective on the city and go to the more “off the beaten path” sides of Chicago. Imagine delving into the landmarks of Chicago’s music history on our Jazz, Blues and Beyond tour, which goes to neighborhoods north to south. Our Neighborhoods and Cultural Diversity tour talks about the diverse immigrant groups and communities that have made our city great, and you get to see historic homes, colorful murals, and a vast mix of landscapes.

Private Tour Chicago Tesla
I mean, c’mon. Photo Courtesy of Greenlux Chicago

4. You want to take a tour in PEAK comfort

Whether by foot or vehicle, our small group private tours are tailored to your comfort. Want to add a stop for coffee on our Loop Interior Architecture Walking Tour? We can do that. Or, if you’re taking a tour via car, it might as well be a luxury vehicle.

Groups of one to three guests enjoy taking in the highlights of Chicago architecture from the comfort of a Tesla. With panoramic windows that reach all the way to the backseat and no(!) engine, you’ll be able to easily hear and see everything on your tour. On top of all that, these cars have the highest safety rating in the world AND lift doors.

“[Riding in a Tesla] is a sustainable experience with a touch of luxury. It is a car that feels good to be in,” said Mark, owner of Greenlux Chicago, our preferred provider for small group tours by car.

5. Vous préfériez une tournée en français / Preferisci un tour in italiano

We offer tours in French (courtesy of tour guide Elizabeth Tieri who studied at the Sorbonne) or Italian (courtesy of our own Executive Director Amanda Scotese). Whether a brief, deux-heures (2-hour) tour, or a full day di otto ore (8-hour) Chicago experience–we’ve got you covered in three different languages.

Private Tour Coordinator Morgan Lott


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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